Methyl chloroformate → HCID 86746184, compound
Reaction equation
[NH2:1][C@@H:2]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:21][CH:20]=1)[C:3]([NH:5][C:6]1[C:11]([CH:12]([CH3:14])[CH3:13])=[CH:10][CH:9]=[CH:8][C:7]=1[CH:15]([CH3:17])[CH3:16])=[O:4].C(N(CC)CC)C.[CH3:40][O:41][C:42](Cl)=[O:43]>C1COCC1>[CH3:17][CH:15]([C:7]1[CH:8]=[CH:9][CH:10]=[C:11]([CH:12]([CH3:14])[CH3:13])[C:6]=1[NH:5][C:3](=[O:4])[C@@H:2]([NH:1][C:42](=[O:43])[O:41][CH3:40])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[CH:21][CH:20]=1)[CH3:16]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a coded (0° C.) solution of (S)-α-amino-N-[2,6-bis(1-Methylethyl)phenyl]-4-(phenylmethoxy)benzenepropanamide (4.50 g, 10.5 mmol) and triethylamine (1.75 mL, 12.5 mmol) in THF (125 mL) was added methylchloroformate (0.97 mL, 12.5 mmol). The resulting slurry was stirred (1 hr, 0° C.) then filtered, and the filtrate was concentrated. The residue was taken up in ethyl acetate (300 mL), washed with water (1×mL), washed with saturated sodium bicarbonate (1×100 mL), washed with brine (1×100 mL), then dried (MgSO4) and concentrated in vacuo. The resulting solid was recrystallized from ethyl acetate to yield 3.0 g (59%) of the title compound, mp 179°-182° C.
Workup
- filtrationthen filtered
- concentrationthe filtrate was concentrated
- washwashed with water (1×mL)
- washwashed with saturated sodium bicarbonate (1×100 mL)
- washwashed with brine (1×100 mL)
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
- customThe resulting solid was recrystallized from ethyl acetate
Sources & evidence
- ORD record
- ord-451ef65379054cd990d5c35f3bb91de2
- Source dataset
- uspto-grants-1992_10
- Patent number
- US05153226
Reaction notes
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